The first pitch

I have recently gone through the throes of pitching twice.  The first was at the Banff Venture Forums BootCamp (hosted by Innovate Calgary and sponsored primarily by PwC).  It was a real elevator pitch... no powerpoints, and a short, strict time limit.

Boy, did I choke.  I wasn't the only one, but it was a good lesson:  You will choke on your first pitch.
More importantly, it was the best environment for a good lesson: I pitched in front of those who had forged ahead and had both failed and succeeded, as well as peers at all stages of their venture.  None were critical, but all had good advice to incorporate into my pitch.  For example: mine has an excellent story that many Canadians can associate with.

The second was at the University in my Intro to Entrepreneurship course, with Patrick Lor as the guest panelist.  This time I nailed it.  I had my powerpoint this time to help me along, plus the advice from BVF Bootcamp.  I nailed it in terms of presentation, though had some content lacking.  This time, I got loads of good feedback to incorporate into my pitch as I gear up for a real pitch situation.

The point is, your first pitch should never be in front of your actual target audience.  Use all the tactics of mirror-pitching, family-pitching and friends-pitching... and then pitch to a room of strangers that are amicable to your situation.  This puts you in a constructive yet uncomfortable situation.  Get comfortable in that space, and you're ready to hit your targets (or at least, light-years ahead of where you would have been otherwise).